101 things to do in New York: Your essential guide to Gotham

Kayak for free

• Free

New York City isn’t surrounded by water for nothing. During the warmer months, organizations across Gotham offer gratis kayaking time to any and all, from Red Hook to Long Island City. We’ve put together a list of spots where you can swing a paddle by your lonesome or go out on group treks, all free of charge.

Head to a concert in Central Park

Between June and late August, the folks behind SummerStage (which celebrates its 28th season this year) present a huge lineup of outdoor gigs in parks throughout the five boroughs. The SummerStage Mainstage has the most swoonworthy setting, nestled in the middle of quiet Central Park and surrounded by leafy trees. During summer 2012, big-ticket draws included Norah Jones, Beach House and M83—and free shows by the likes of Alabama Shakes, Dawes and other notable acts often went down.

Listen to ace storytellers

• Price band: 1/4
• Critics choice

Ten tales. Three teams of judges. One winner. The Moth’s StorySLAM event, the outrageously (and deservedly) popular, spontaneous reading series (held every few weeks in a variety of venues throughout the city), pits local scribes against one another, challenging them to come up with an impressive work based on a specific theme. Get in line early, as spots for writers and spectators alike go quickly. And discover more of our favorite unscripted sessions in our handy list.

See a drag show

Looking for a night of naughty fun? Check out one of these queer parties. On Wednesdays, The Sherry Vine Show brings brilliant song parodies and acid wit to Hell’s Kitchen hot spot Industry Bar. Come Saturday, join wisecracking host Linda Simpson at Le Poisson Rouge’s Le Bingo throwdown, where you can battle for cool prizes. And cap off your weekend on Sundays with some infused vodka and a performance from the tireless Paige Turner at Vlada Lounge.

Indulge in decadent cocoa creations during the Hot Chocolate Festival

• Price band: 1/4
• Critics choice

City Bakery’s annual monthlong hot-chocolate festival is a bacchanal of cream, chocolate and homemade marshmallows. Starting Feb 1, a different flavor of the potent stuff will be served daily. You’ll be able to peep the full calendar of flavors on the bakery’s site starting Jan 21.

Eat and drink at the movies

The current king of NYC eat-and-booze cinemas (for now—the massive Alamo Drafthouse opens in Downtown Brooklyn in 2015, and then the jury will be out), Williamsburg’s Nitehawk Cinema serves themed top-shelf cocktails and eats during first-run showings. The theater also programs old faves, brunch and midnight screenings, bands playing over experimental shorts by locals, and viewings that include a beer-pairing dinner. At the reRun Gastropub Theater in Dumbo, you can settle into a repurposed car seat and order craft brews, wine and pub grub while enjoying indies by up-and-coming auteurs.

Explore the city’s literary bars

Booze and books have had a long, well-documented relationship—especially in New York. Nab a stool at Kettle of Fish (59 Christopher St between Seventh Ave South and Waverly Pl; 212-414-2278, kettleoffishnyc.com), where Beat Generation heavyweights Allen Ginsberg and Jack Kerouac tipped back a few in the ’50s and ’60s. Or grab a pint at Old Town Bar (5 E 18th St between Broadway and Park Ave South; 212-529-6732, oldtownbar.com), a favorite watering hole of Frank McCourt and Nick Hornby. For more of the best literary bars in town, check out our roundup.

Enjoy world music at Barbès

• Price band: 1/4

This cozy bar in Park Slope hosts one of the city’s liveliest, most diverse music scenes in its cramped but friendly back room. Separated from the well-stocked front bar by a humble curtain, you might encounter indie rock, progressive jazz, classical chamber music, West African funk, French musette…you name it. Don’t miss the fun-as-hell collective Slavic Soul Party!, which brings Eastern European jams to the space every Tuesday (9pm; $10).

Check out the New York International Fringe Festival

Every August, theatergoers brace themselves for this envelope-pushing fest. It hits us in the dog days of summer like a punishing heat wave of talent—or, if not talent, then unbridled, reckless enthusiasm. First mounted in 1997 out of a few poky Off-Off Broadway spaces on the Lower East Side, the Fringe has grown in size and cultural cachet. Now it calls itself “the largest multiarts festival in North America,” with yearly attendance topping 75,000. Visit our NYIFF page in early August for the full lineup. Prices vary; see fringenyc.org for details.

Get down at Mister Saturday Night

Justin Carter and Eamon Harkin’s bimonthly party, held at spaces throughout the city, is devoted to the outer reaches of house, disco and techno. The duo’s ethos is one of community and coming together, along with, of course, hard-grooving fun. Past guest DJs have included Four Tet, Greg Wilson and Floating Points. Click here to read our interview with Carter and Harkin. Visit mistersaturdaynight.com for more information. Prices vary.